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T1912

Sigma-Aldrich

Paclitaxel

from Taxus yannanensis, powder

Empirical Formula (Hill Notation):
C47H51NO14
CAS Number:
Molecular Weight:
853.91
Beilstein:
1420457
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

Taxus yannanensis

form

powder

color

white

mp

213 °C (dec.) (lit.)

solubility

DMSO: 50 mg/mL (can be stored frozen for several months)
acetonitrile: soluble
ethanol: soluble
methanol: soluble (undergoes transesterification)

antibiotic activity spectrum

neoplastics

Mode of action

DNA synthesis | interferes

originator

Bristol-Myers Squibb

storage temp.

2-8°C

SMILES string

[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](OC(C)=O)C4=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)c5ccccc5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)c6ccccc6)c7ccccc7

InChI

1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1

InChI key

RCINICONZNJXQF-MZXODVADSA-N

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General description

Chemical structure: taxoide

Application

Paclitaxel has been used to study PREP2-tubulin interactions using coimmunoprecipitation assays on NIH3T3 cell extracts. This drug has also been used to stabilize tubulin obtained from pig brain.

Packaging

1, 5, 25 mg in glass bottle

Biochem/physiol Actions

Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).

Features and Benefits

This compound was developed by Bristol-Myers Squibb. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Caution

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

Preparation Note

Paclitaxel is soluble in DMSO at 50 mg/ml and can be stored frozen for several months. It is also soluble in methanol (undergoes transesterification), acetonitrile and ethanol. Paclitaxel is rapidly destroyed in weakly alkaline, methanolic solutions and in strongly acidic methanolic solutions (1:1 of methanol:concentrated HCl). It is also soluble in a mixture of 50% Cremophor EL and 50% anhydrous ethanol.

Signal Word

Danger

Hazard Classifications

Eye Dam. 1 - Muta. 1A - Repr. 1A - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

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Product Information Sheet

More Documents

Quotes and Ordering

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